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Homovanillin

PubChem CID
151276
Structure
Homovanillin_small.png
Homovanillin_3D_Structure.png
Molecular Formula
Synonyms
  • 2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
  • Homovanillin
  • 5703-24-2
  • (4-Hydroxy-3-methoxyphenyl)acetaldehyde
  • HMPAL
Molecular Weight
166.17 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-11
Description
(4-hydroxy-3-methoxyphenyl)acetaldehyde is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes. It has a role as a human metabolite and a mouse metabolite.
Homovanillin has been reported in Picea abies and Homo sapiens with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Homovanillin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C9H10O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,5-6,11H,4H2,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GOQGGGANVKPMNH-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC1=C(C=CC(=C1)CC=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C9H10O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 HMDB ID

2.3.6 KEGG ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 PharmGKB ID

2.3.10 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (4-hydroxy-3-methoxyphenyl)acetaldehyde
  • HMPAL
  • homovanillin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
166.17 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
166.062994177 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
166.062994177 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
46.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
147
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Kovats Retention Index

Standard non-polar
1406 , 1418.9
Semi-standard non-polar
1458.1 , 1461.9
Standard polar
2528.2

5 Chemical Vendors

6 Food Additives and Ingredients

6.1 Associated Foods

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Cellular Locations

Cytoplasm

7.1.2 Metabolite Pathways

7.2 Biochemical Reactions

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Thieme References

8.5 Chemical Co-Occurrences in Literature

8.6 Chemical-Gene Co-Occurrences in Literature

8.7 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Interactions and Pathways

10.1 Pathways

11 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

12 Classification

12.1 MeSH Tree

12.2 ChEBI Ontology

12.3 ChemIDplus

12.4 NORMAN Suspect List Exchange Classification

12.5 EPA DSSTox Classification

12.6 LOTUS Tree

12.7 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    (4-Hydroxy-3-methoxyphenyl)acetaldehyde
    https://comptox.epa.gov/dashboard/DTXSID70205641
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  6. ChEBI
  7. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  8. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  9. Japan Chemical Substance Dictionary (Nikkaji)
  10. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  11. KNApSAcK Species-Metabolite Database
  12. Natural Product Activity and Species Source (NPASS)
  13. Metabolomics Workbench
  14. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Ethanal, 2-(4-hydroxy-3-methoxyphenyl)
    http://www.nist.gov/srd/nist1a.cfm
  15. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  16. Springer Nature
  17. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  18. Wikidata
    (4-hydroxy-3-methoxyphenyl)acetaldehyde
    https://www.wikidata.org/wiki/Q27103508
  19. PubChem
  20. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    (4-hydroxy-3-methoxyphenyl)acetaldehyde
    https://www.ncbi.nlm.nih.gov/mesh/67050963
  21. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
  24. NCBI
CONTENTS